Dichloromethane → HCID 71257931, compound

Participants

Reaction Steps

In a 250 mL round-bottomed flask, 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(5-(methylsulfonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde (154 mg, 256 μmol, Eq: 1.00) was combined with dichloromethane (24 ml) and 2 mL MeOH. Sodium borohydride (14.5 mg, 383 μmol, Eq: 1.5) was added and the reaction suspension was stirred at ambient temperature for 1 h. 1 mL of saturated NH4Cl was added; followed by 5 mL H2O. The mixture was stirred for 5 min. The reaction mixture was poured into 50 mL H2O and extracted with dichloromethane (3×50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 1% to 3% MeOH in DCM) to afford the desired product (90 mg) as a white powder. (M+H)+=605 m/e. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H) 3.10 (s, 3 H) 3.77 (s, 3 H) 4.51 (br. s., 2 H) 6.94 (d, J=8.59 Hz, 1 H) 7.48-7.65 (m, 3 H) 7.88 (d, J=2.53 Hz, 1 H) 8.00 (dd, J=8.59, 2.53 Hz, 1 H) 8.33-8.45 (m, 2 H) 8.71 (d, J=5.05 Hz, 1 H) 8.82 (d, J=2.53 Hz, 1 H) 8.92 (d, J=2.53 Hz, 1 H).

Provenance & Evidence